Organogels Based on J- and H-Type Aggregates of Amphiphilic Perylenetetracarboxylic Diimides

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• 作者：Haixia Wu ; Lin Xue ; Yan Shi ; Yanli Chen ; Xiyou Li
• 刊名：Langmuir
• 出版年：2011
• 出版时间：March 15, 2011
• 年：2011
• 卷：27
• 期：6
• 页码：3074-3082
• 全文大小：1052K
• 年卷期：v.27,no.6(March 15, 2011)
• ISSN：1520-5827

文摘

Three new perylenetetracarboxylic diimide (PDI) compounds substituted with hydrophobic and/or hydrophilic groups at the two imide nitrogen positions, namely N,N鈥?di[N-(4-aminophenyl)-3,4,5-tris(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzamide]-1,7-di(4-tert-butylphenoxy)perylene-3,4;9,10-tetracarboxylic diimide (1), N,N鈥?di[N-amido-3,4,5-tris(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzamide]-1,7-di(4-tert-butylphenoxy)perylene-3,4;9,10-tetracarboxylic diimide (2), and N-amido-3,4,5-tris(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)benzamide-N鈥?amido-3,4,5-tris(dodecyloxy)benzamide-1,7-di(4-tert-butylphenoxy)perylene-3,4;9,10-tetracarboxylate diimide (3), have been designed and prepared. The gelating abilities of them in different solvents have been investigated, and the results indicated that compounds 1 and 3 can form fluorescent gels whereas compound 2 cannot. The properties of the gels of compounds 1 and 3 have been investigated by UV鈭抳is absorption and emission spectra. The results indicate that the gel of compound 1 is composed of H-aggregates, whereas the gel of compound 3 is composed of J-aggregates. The reversible transformation between gel and solution states induced by temperature change is observed. The structure of dried gel has been investigated by X-ray diffraction (XRD) experiments, and the morphology has been measured by atomic force microscopy (AFM). This research revealed successfully the crucial roles of amphiphilic properties and the side-chain conformations in controlling the gelating properties of PDI molecules. This information may be useful for the design of novel organogels based on perylenetetracarboxylic diimides.